Man Ningning, Li Yuming, Jie Jiyang, Li Hongyun, Yang Haijun, Zhao Yufen, Fu Hua
Key Laboratory of Bioorganic Phosphorus Chemistry and Chemical Biology (Ministry of Education), Department of Chemistry, Tsinghua University, Beijing, 100084, China.
Chemistry. 2021 Sep 6;27(50):12884-12889. doi: 10.1002/chem.202102040. Epub 2021 Jul 22.
Chiral phosphoric acid-catalyzed couplings of C-alkynyl N,N'-di-(tert-butoxycarbonyl)-aminals with β-naphthols led to chiral propargylamines in moderate to high yields with high to excellent enantioselectivity, in which the reactions underwent sequential chiral phosphoric acid-catalyzed in situ formation of N-(tert-butoxycarbonyl)-imines (N-Boc-imines) from the aminals, and 1,2-addition of β-naphthols to the N-Boc-imines. Chiral 1,2-dihydronaphtho[2,1-b]furans and naphtho[2,1-b]furans were prepared with satisfactory results when 10 mol% AgOAc and 20 mol% 2,6-lutidine or 1.2 equiv. of 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) were added to the resulting chiral propargylamines solution, respectively.
手性磷酸催化的C-炔基N,N'-二（叔丁氧羰基）-氨缩醛与β-萘酚的偶联反应以中等到高的产率、高到优异的对映选择性生成手性炔丙胺，其中反应经历了手性磷酸催化氨缩醛原位形成N-（叔丁氧羰基）-亚胺（N-Boc-亚胺），以及β-萘酚对N-Boc-亚胺的1,2-加成。当分别向所得手性炔丙胺溶液中加入10 mol%醋酸银和20 mol% 2,6-二甲基吡啶或1.2当量的1,8-二氮杂双环[5.4.0]十一碳-7-烯（DBU）时，制备出手性1,2-二氢萘并[2,1-b]呋喃和萘并[2,1-b]呋喃，结果令人满意。
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